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It's looking good rwaluchow. I like how you shifted the market to the main thoroughfair and have placed (what I assume) are large mansions/public buildings on the path leading to the castle. The crumbling wall and the fields around the settlement look much more natural now.

If you don't mind a few more brickbats , there were a few more things you might want to keep in mind. Again, these criticisms are from a realism standpoint (which is relative in a world with fireballs and dragons) and from the study of history and urban planning. If you look hard enough, you can find examples to prove almost anything, so take these with a grain of salt.

While your medieval city should not have an American style road grid (most European cities had their road grids grow from old cattle and foot paths as well as being shaped by the landforms around them (streams, hills, etc.), you should have a straighter road on the south side of town connecting the two sides of the city (just as the northside has).

There are many examples of roads with crazy layouts, but I suspect a major artery connecting two halves of the city would be more curving and have less 90 degree turns. Hyper efficient road planning like you find in the interstate system and many American downtowns was not a priority in the middle ages, but the people of the time did know the basics of how to keep foot, horse, and cart traffic flowing to and through a city.

Second, while I like the outbuildings beyond the wall (and given that the wall is crumbling, I assume whatever threat the city was settled for has been quelled), kill what I call "tv antennas". What do I mean by that? You've got buildings on streets outside the city that fork and go nowhere. For instance, in the nw part of the map outside the walls, there is a crossroads with buildings on it and one half of the crossroads doesn't go anywhere and deadends--that looks unrealistic. Meanwhile, the ne gate has structures near it, but there are also open areas nearby--unrealistic unless its been cleared for defensive reasons or there's a market/meeting area outside the gates. Most outbuildings in the middle ages tended to cluster and grow out from the gates/entrances/access points (or sites of former gates) that lead into a city.

The best way to think of a medieval city (or a modern one) is a living organism akin to a tree. The organism grows in rings outward. Just as most trees found in nature are not perfectly cylindrical, so the outer growth of a city will be uneven. Have a few densely built up blocks near the entranceways and then thin out the structures as you get further away from the city. Genuine crossroads near a city will sometimes be built up, but most of the structures will be near the entrances.

I hope you find some use out of my advice rwaluchow. Your map looks great as it is, I hope you don't mind if I snag it for a future adventuring session or two

I like it. You've done a nice job with the layout of the streets and such, it is compact, but that is certainly no sin in a setting where you have castles and walls and nasty things outside that want to get inside.

This is not so much a critique as a question: do you want to make some of the buildings inside of the walls connected to one another? The reason that I say this is that you do find some buildings made in that fashion in this style of map, pushed rather tightly against one another. It diesn;t have to be all either, in fact better if it is not IMHO.